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26412-87-3 - Sulfur trioxide-pyridine complex, 98%, active SO3 ca 48-50% - Pyridine-sulfur trioxide complex - A12202 - Alfa Aesar

A12202 Sulfur trioxide-pyridine complex, 98%, active SO3 ca 48-50%

Numéro CAS
26412-87-3
Synonymes
Pyridine-sulfur trioxide complex

Dimensions Prix ($) Quantité Disponibilité
10g 15,28
50g 45,01
250g 171,00
1000g 420,80
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Sulfur trioxide-pyridine complex, 98%, active SO3 ca 48-50%

MDL
MFCD00012437
EINECS
247-683-3

Propriétés chimiques

Formule
C5H5NO3S
Poids formulaire
159.16
Point de fusion
ca 155-165°
Sensibilité
Moisture Sensitive
Solubilité
Soluble in polar organic solvents.

Applications

Sulfur trioxide-pyridine complex is used for sulfations of alcohols, sulfonations, deoxygenations and other reductions, oxidations with dimethyl sulfoxide. It is also used as a source of sulfur trioxide especially in the preparation of sulfate esters. Further, it is used as an activating electrophile in a Parikh-Doering oxidation. In addition to this, it is also used in the preparation and anticoagulation test of sulfated silk fibroin.

Notes

Moisture sensitive. Incompatible with strong oxidizing agents.

Références bibliographiques

Converts alcohols to monoalkyl sulfates, utilized in carbohydrate protection: Carbohydr. Res., 127, 211, 131, C8 (1984); J. Org. Chem., 38, 3510 (1973). The pyridinium sulfates of allylic or benzylic alcohols can be deoxygenated in high yields by in situ LiAlH4 reduction in THF: J. Org. Chem., 34, 3667 (1969); Tetrahedron Lett., 4650 (1972); J. Am. Chem. Soc., 93, 7016 (1971).

Sulfonates indole at the 3-position: Tetrahedron, 29, 669 (1973).

The combination with Dimethyl­ sulfoxide, A13280, is a mild oxidant for alcohols to carbonyl compounds (Parikh-Doering Reagent): J. Am. Chem. Soc., 89, 5505 (1967), avoiding the very low temperatures required for the Swern and similar systems (see Oxalyl­ chloride, A18012). With chiral alcohols, less racemization occurs at the ɑ-carbon than with Collins' reagent or pyridinium dichromate: Tetrahedron Lett., 23, 807 (1982); J. Org. Chem., 46, 4799 (1981). Nicolaou utilized the system at 0oC to convert an epoxy alcohol to the corresponding aldehyde in the synthesis of hemibrevitoxin B: J. Am. Chem. Soc., 115, 3558 (1993).

In combination with NaI, reduces ɑ-halo ketones to ketones: Synthesis, 59 (1979), and sulfoxides to sulfides: Synthesis, 984 (1979).

Lim, D. K.; Wylie, R. G.; Langer, R.; Kohane, D. S. Selective binding of C-6 OH sulfated hyaluronic acid to the angiogenic isoform of VEGF165. Biomaterials 2016, 77, 130-138.

Sarbova, V.; Koschella, A.; Cheng, F.; Kelly, S. M.; Heinze, T. Studies on the sulfation of cellulose alpha-lipoate and ability of the sulfated product to stabilize colloidal suspensions of gold nanoparticles. Carbohydr. Polym. 2015, 124, 117-123.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H314-H318-H302

Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if swallowed.

Mentions de prudence: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P301+P312-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3704116
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2933.39
TSCA
Yes

Recommandé

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Catalyseurs

Analytique et matériel de laboratoire